A Photoinduced dearomative nucleophilic addition to N-Boc indoles mediated by two-molecule organic photoredox catalysts such as phenanthrene and 1,4-dicyanobenzene with UV irradiation furnished 2-substituted indolines in moderate quantitative yields. Hydroxide, alkoxide, cyanide ions can be used a nucleophile provide 2-hydroxy, 2-alkoxy, 2-cyanoindolines, respectively. Both electron-rich -defic...